Efficient Synthesis by Mono-Carboxy Methylation of 4,4′-Biphenol, X-ray Diffraction, Spectroscopic Characterization and Computational Study of the Crystal Packing of Ethyl 2-((4′-hydroxy-[1,1′-biphenyl]-4-yl)oxy)acetate

Abstract

Herein, mono-carboxy methylation of 4,4′-Biphenol was accomplished to give ethyl 2-((4′-hydroxy-[1,1′-biphenyl]-4-yl)oxy)acetate (EBPA). The chemical structure of EBPA was determined using single crystal XRD and characterized by FT-IR, UV-Visible, 1H-NMR, EIMS and elemental analysis. Additionally, computational studies of EBPA were performed using density functional theory (DFT) at M06-2X/6-311+G(d,p) and B3LYP/6-311+G(d,p) levels of theory to get optimized structures and countercheck the experimental findings. Overall, DFT findings at M06-2X/6-311+G(d,p) level show good concurrence with the experimental data which confirms the purity of EBPA. Frontier molecular orbital (FMO), molecular electrostatic potential (MEP), natural bond orbital (NBO) analysis and nonlinear optical (NLO) properties were explored at M06-2X/6-311+G(d,p) level of theory. UV-Vis analysis at TDDFT/M06-2X/6-311+G(d,p) level of theory showed that experimental absorption wavelength was in good agreement with DFT calculated absorption wavelength. NBO analysis disclosed that hyperconjugative interactions and hydrogen bonding network are responsible for the stability of EBPA. The global reactivity parameters indicate that EBPA holds more donating capability and stability. The NLO results were observed better than standard molecule recommended the NLO activity of EBPA. We hope that this synergistic experimental-computational study may provide new ways for the utilization of EBPA as NLO material for hi-tech applications.